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| Names | |
|---|---|
| Preferred IUPAC name Disodium (12S,14aR,15aS,16aR,17aS,18Z,110aR,111aS,112aR,113aS,114aR,116R,117R,118aS,119aR,121aS,122aR,123aS,124aR,125aS,126aR,127aS,22S,24aR,25aS,26aR,27aS,28aR,29aS,211R,212R,213aR,214S,214aS,215aR,217aS,218aR,219aS,32R,33R,34aS,36S,37R,38R,38aS,5R,7R,82S,83R,84aS,86R,87R,88R,88aS,92R,93R,94R,94aS,95aS,96aR,97aS,98R,99R,910S,911aR,912aS,913aR,914R,914aR,11S,12R,132S,133R,134S,134aS,135aR,136aS,137aR,138S,138aS,1310S,1311R,1312aR,1313aS,1314aR,1315aS,1317R,1317aR)-12-[(1S,2R,4R,5S)-1,2-dihydroxy-4,5-dimethyloct-7-en-1-yl]-117,211,214,33,37,38,5,7,83,87,88,93,94,98,914,11,12,133,134,138,1311,1317-docosahydroxy-14a,15a,16a,114a,116,119a,121a,122a,25a,27a,29a,214a,217a,1313a,1315a-pentadecamethyl-132-[(2R,3R,4R,7S,8R,9R,11R,13E)-3,8,11,15-tetrahydroxy-4,9,13-trimethyl-12-methylidene-7-(sulfonatooxy)pentadec-13-en-2-yl]-13,14,14a,15a,16,16a,17a,110,110a,111a,112,112a,113a,114,114a,116,117,118,118a,119a,120,121,121a,122a,123,123a,124a,125,125a,126a,127,127a,22,23,24,24a,25a,26,26a,27a,28,28a,29a,210,211,212,213a,214,214a,215a,216,217,217a,218a,219,219a,32,33,34,34a,36,37,38,38a,82,83,84,84a,86,87,88,88a,93,94,94a,95a,96,96a,97a,98,99,910,911a,912,912a,913a,914,914a,133,134,134a,135a,136,136a,137a,138,138a,1310,1311,1312,1312a,1313a,1314,1314a,1315a,1316,1317,1317a-octahectahydro-12H,92H,132H-1(16)-pyrano[2′′′ ′,3′′′ ′:5′′′,6′′′]pyrano[2′′′,3′′′:6′′,7′′]oxepino[2′′,3′′:5′,6′]pyrano[2′,3′:5,6]pyrano[3,2-b]pyrano[2′′′,3′′′:5′′,6′′]pyrano[2′′,3′′:5′,6′]pyrano[2′,3′:5,6]pyrano[2,3-g]oxocina-2(2,12)-bis(pyrano[2′′,3′′:5,6]pyrano[2′,3′:5,6]pyrano)[3,2-b:2′,3′-f]oxepina-13(10)-pyrano[3,2-b]pyrano[2′′′,3′′′:5′′,6′′]pyrano[2′′,3′′:5′,6′]pyrano[2′,3′:5,6]pyrano[2,3-f]oxepina-9(2,10)-dipyrano[2,3-e:2′,3′-e′]pyrano[3,2-b:5,6-b′]dipyrana-3,8(2,6)-bis(pyrano[3,2-b]pyrana)tridecaphan-99-yl sulfate | |
| Identifiers | |
3D model (JSmol) | |
| ChEMBL | |
| ChemSpider |
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| ECHA InfoCard | 100.227.039 |
| KEGG | |
| UNII | |
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| Properties | |
| C164H256O68S2Na2 | |
| Molar mass | 3422 g/mol |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Maitotoxin (MTX) is an extremely potenttoxin produced byGambierdiscus toxicus, adinoflagellate species. Maitotoxin has been shown to be more than one hundred thousand times as potent as the nerve agentVX.[1][improper synthesis?] Maitotoxin is so potent that it has been demonstrated that anintraperitoneal injection of 130ng/kg was lethal in mice.[2] Maitotoxin was named from theciguateric fishCtenochaetus striatus—called "maito" inTahiti—from which maitotoxin was isolated for the first time. It was later shown that maitotoxin is actually produced by the dinoflagellateGambierdiscus toxicus.
Maitotoxin activatescalcium channels, leading to an increase in levels of cytosolic Ca2+ ions.[3] The exact molecular target of maitotoxin is unknown, but it has been suggested that maitotoxin binds to theplasma membrane Ca2+ ATPase (PMCA) and turns it into anion channel, similar to howpalytoxin turns theNa+/K+-ATPase into asodium channel.[4] Ultimately, anecroptosis cascade is activated, resulting inmembrane blebbing and eventuallycell lysis.[5][6] Thetoxicity of maitotoxin in mice is the highest for nonprotein toxins: theLD50 is 50 ng/kg.[7]
Themolecule itself is a system of 32 fused rings and is notable for being one of the largest and most complex non-protein, non-polysaccharide molecules produced by anyorganism. Maitotoxin includes 32ether rings, 22methyl groups, 28hydroxyl groups, and 2sulfuric acidesters and has anamphipathic structure.[8][9][10] Its structure was established through analysis usingnuclear magnetic resonance atTohoku University,Harvard University and theUniversity of Tokyo in combination withmass spectrometry, and synthetic chemical methods. However, Andrew Gallimore and Jonathan Spencer have questioned the structure of maitotoxin at a single ring-junction (the J–K junction), based purely on biosynthetic considerations and their general model for marine polyether biogenesis.[11]K. C. Nicolaou and Michael Frederick argue that despite this biosynthetic argument, the originally proposed structure could still be correct.[12] The controversy has yet[needs update] to be resolved.
The molecule is produced in nature via apolyketide synthase pathway.[11]
Since 1996 the Nicolaou research group is involved in an effort to synthesise the molecule viatotal synthesis[13][14][15][16] although as of 2015 the project is on hold due to lack of funding.[17]
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